Rupert is a character featured in Fable II. He is the son of Giles, a former guard turned farmer, and Jennifer. Originally from Bowerstone, Giles moved his family to Brightwood to start a farm. Unfortunately, shortly after relocating, Giles and his family began to be tormented by the bandit Ripper and his clan.

When the trouble started, Giles sent Rupert to Bowerstone so he would be safe. While he was away, Rupert's mother, Jennifer, was killed during one of Ripper's raids by a thug named Ethan.

If the Hero helped Giles, then, upon returning from the Spire, then the Hero will find that in the past 10 years Giles has flourished, his farm growing into a small settlement. He asks the Hero of another favour: help his son find a wife, thus starting The Blind Date quest. Upon talking to Rupert, in order to find out his ideal woman, Rupert reveals that he is not interested in girls and is, in fact, a homosexual. The Hero can choose to try to find a wife anyway, for evil points, or attempt to find a suitable husband, for good points. Either way, upon returning Rupert comes out to his father. Giles is happy for his son and agrees to move to Bowerstone with him, and the pair are never seen again.

Rupert and his father are a clear reference to the character of Rupert Giles, played by Anthony Stewart Head, from the American television series Buffy the Vampire Slayer. Firstly, Giles and his son's name combined make the character's name. Secondly, as a youth, Rupert Giles operated under the moniker of "Ripper", the name given to the bandit that terrorises Giles and his family. The name of Rupert's deceased mother is Jennifer, referring to Rupert Giles' love interest Jenny Calendar, played by Robia LaMorte, who also meets a premature end.

Rupert is a "closet" homosexual, preferring to hide his situation from his father. This is rather strange since homosexuality is accepted in Albion and is a possible choice by the player concerning their Hero. Same sex relationships and marriage is possible and widely accepted, though some NPCs still express homophobia. His father, wanting Rupert to marry a woman, potentially represents this homophobia, or, at least, the heteronormative impulse of society. The Hero has the ability to find Rupert a suitable partner. Once a suitable husband has been found, Rupert confesses his homosexuality to his father. Giles accepts Rupert and they go to live in Bowerstone with Rupert's husband.